1. Field of the Invention
This invention relates to new octyl ethers and octadienyl ethers.
2. Statement of Related Art
It is known in the art that conjugated dienes can telomerize with alcohols to give 1,7- and 2,7-alkadienyl ethers. The following references examplify extensive patent and other literature that relate to such telomerization reactions and novel compounds prepared by such reactions: U.S. Pat. Nos. 3,489,813; 3,499,042; 3,670,032; 3,769,352; 3,792,101; 3,887,627; 3,891,684; 3,923,875; 3,992,456; 4,006,192; 4,142,060; 4,146,738; 4,196,135; 4,196,135; 24,219,677; 4,260,750; 4,356,333; 4,417,079; 4,454,333; 4,515,711; 4,522,760; and 4,642,392. British Patent Nos. 1,248,592; 1,248,593; 1,354,507; 2,054,394; and 2,114,974. German Patent Nos. 1,807,491; 2,154,370; and 2,505,180. Japanese Patent Nos. 72,020,604; 47,031,906; 48,039,413; 73,042,606; 73,003,605; 49,031,965; 49,048,613; 49,125,313; 74,046,286; 50,157,301; 51,008,206; 51,142,532; 51,149,206; and 51,007,426. Literature articles: Behr, Organometallics 5, 514-8 (1986) Jolly, Organometallics 5, 473-81 (1986) Dzhemilev, Zh. Org. Khim. 22 (8), 1591-7 (1986) Gaube, J. Prakt. Chim. 327 (4), 643-8 (1985) Jolly, Organometallics 4, 1945-53 (1985) Bochmann, J. Molec. Catalysis 26, 79-88 (1984) Behr, Aspects of Homogneous Catalysis 5, 5-58 (1984) Gaube, J. Prakt. Chem. 326, (6) 947-54 (1984) Behr, Chem. Ber. 116, 862-73 (1983) Groult, Tetrahedron 39, (9) 1543-50 (1983) Teranishi, J. Org. Chem. 46, 2356-62 (1981) Dzhemilev, Izv. Akad. Nauk. SSSR, Ser. Khim. 8, 1837-425 (1981) Keim, J. Molec. Catalysis 10, 247-252 (1981) Dzhemilev, Zh. Org. Khim. 16 (6), 1157-61 (1980) Yoshida, Tetr. Letters 21, 3787-90 (1980) Tsuji, Pure & Appl. Chem. 51, 1235-41 (1979) Tsuji, Adv. in Organometallic Chem. 17, 141-93 (1979) Singer, J. Organomet. Chem. 137 (3), 309-14 (1977) Chauvin, Tet. Letters 51, 4559-62 (1975) Chauvin, Bull. Soc. Chim. Fr. 652-6 (1974) Beger, J. Prakt. Chem. 315 (6), 1067-89 (1973) Baker, Chemical Reviews 73 (5), 503-9 (1973) Tsuji, Accounts Chem. Res. 6 (1), 8-15 (1973) Smutny, Annals N.Y. Acad. Sci. 214, 124-142 (1973) Chauvin, Tetr. Letters 51, 4559-62 (1973) Rose, J. Organometallic Chem. 49, 473-6 (1973) Smutny, ACS, Div. Petr. Chem., Prepn. 14 (2), B100-11 (1969) Takahashi, Bull. Chem. Soc. Japan 41, 254-5 (1968) Takahashi, Bull. Chem. Soc. Japan 41, 454-60 (1968) Smutny, J. Am. Chem. Soc. 89, 6793-4 (1967) Takahashi, Tetr. Letters (26), 2451-3 (1967). Lactic and tartaric acids are included in a list of preferred carboxylic acids which can be used to make unsaturated esters of carboxylic acids by reacting the acids with a conjugated diene in the presence of a palladium catalyst in U.S. Pat. No. 3,746,749. The patent contains no teaching or disclosure of how to make any of the claimed alkadienyl esters and/or ethers of the present invention. A copending application Ser. No. 07/517,990 filed on 5/2/90 teaches 1- and 3-substituted octadienyl esters and ethers of hydroxy-substituted carboxylic acids including 2,2-dimethylolpropionic acid. Japanese Patent 7704526 (CA 87: 117573b) teaches the preparation of aminohydroxyoctyl ethers by reaction of diepoxy ethers with amines and alkanolamines. Japanese Patent 7443932 (CA 83:27612b) teaches the preparation of aminohydroxyoctyl fatty esters by aminolysis of 2,3;7,8-diepoxyoctyl fatty esters. U.S. Pat. No. 3,746,749 also teaches that alcohols can be used as solvents in the telomerization of conjugated dienes with carboxylic acids in conjunction with from 0.1 to 10 moles of an alkali metal salt of a carboxylic acid/mole of carboxylic acid. U.S. Pat. No. 3,923,875 teaches an improved process for producing alkadienol esters which comprises reacting a 1,3-conjugated acyclic diolefin wherein the improvement consists of conducting the process in the presence of a palladium or palladium (II) compound and a mononuclear triarylphosphite in which at least one of the aryl radicals is substituted in the ortho position in the absence of a reaction solvent. The patent also teaches that an inert solvent such as benzene, toluene, ethers, and esters can be used. There is no teaching of the use of alcohol solvents. Japanese patent JP 5034002 (CA 86:4946m) teaches the telomerization of 1,3-butadiene with carboxylic acids in the presence of aprotic solvents using palladium acetate. Japanese patent JP 75022530 teaches the telomerization of a conjugated diene with a carboxylic acid in the presence of palladium acetylacetonate/triphenylphosphine in the presence of unspecified polar solvents. Japanese patent JP 7246566 (CA 78:71465b) teaches the telomerization of 1,3-butadiene with carboxylic acids in the presence Pd(II)(Ph.sub.3 P).sub.3 and a solvent such as acetone, diethyl ether, ethyl acetate, THF, and DMF.
Zh. Org. Khim. 19(2), 463 (1983) (CA 98:215363e) teaches the epoxidation of a 2,7-octadienyl ester of acetic acid by t-butyl hydroperoxidemolybdenum hexacarbonyl in benzene at 80.degree. C. to give the corresponding monoepoxide. Japanese Kokai 53/9701 (CA 88:169938q) teaches the epoxidation of a 2,7-octadienyl ester of terephthalic acid with peracetic acid. Japanese patent JP 4837007 (CA 81:78466y) also teaches the epoxidation of a 2,7-octadienyl ester of terephthalic acid with peracetic acid. German patent DE 2143071 (CA 77:20675s) teaches the epoxidation of a 2,7-octadienyl ester of tetrahydrophthalic acid with peracetic acid.
The use of low levels of palladium catalyst in 1,3-butadiene telomerizations is disclosed in British patent No. 2,114,974. This patent teaches that when 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol telomerized with butadiene, about a 61% yield of monoether based on butadiene can be realized by using a molar ratio of catalyst/diene equal to about 1/20,600. The patent also discloses that a large stoichiometric excess of diol is also necessary in order to obtain high yields of the desired monoether product. For best yields of monoether, the above patent also teaches that the optimum catalytic effect is obtained by combining the palladium catalyst with a nickel(II) compound and a base such as a quaternary ammonium hydroxide. The patent also discloses a method of removing the palladium catalyst with ion exchange resins from the reaction mixture after the reaction has been completed. The palladium levels are obviously not low enough to preclude the recovery step; an operation which the present invention eliminates. U.S. Pat. No. 3,746,749 discloses that octadienyl esters of adipic acid can be prepared in 86% yield by employing a molar ratio of Pd/Acid/Butadiene equal to 1/12,300/56,000 and octadienyl esters of fumaric acid can be prepared in 67% yield by employing a molar ratio of Pd/Acid/Butadiene equal to 1/60,000/28,000. However, these low palladium levels are used in conjunction with from 0.1 to 10 moles of an alkali metal salt of a carboxylic acid/mole of carboxylic acid. U.S. Pat. No. 3,518,315 teaches that 2,2-bis(4-(2,7-octadienyloxy)phenyl) propane is formed by the telomerization of 1,3-butadiene with 2,2-bis(4-hydroxyphenyl) propane (bisphenol A) using a palladium (II) catalyst wherein the palladium (II)/bisphenol A/butadiene ration is 1/39/295 at a temperature of 100.degree. C. for 48 hours.